Hydroxyamine hydrochloride → HCID 53780880, compound

HRID 330266Notes

Reaction equation

HRID 330266 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[Na].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[S:18]([CH2:21][C:22]#[N:23])(=[O:20])=[O:19]>CO>[OH:3][N:2]=[C:22]([NH2:23])[CH2:21][S:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 2778444(Naphthalene-2-sulfonyl)acetonitrileHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 53780880HCID 53780880, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to General Procedure A, hydroxylamine hydrochloride (2.26 g, 32.5 mmol), was added in one portion to a solution of NaOMe, freshly prepared from sodium (0.75 g, 32.5 mmol) in methanol. The resulting mixture was stirred 1 hour at room temperature, during which time a precipitate was formed. (2-Naphthalenylsulfonyl)acetonitrile (3.0 g, 13.0 mmol), was added in one portion and the resulting mixture heated to reflux a total of 24 hours. The mixture was cooled to room temperature and then to 0° C. to give a precipitate. The precipitate was collected by filtration, washed with water, and dried in vacuo to give a white crystalline solid (2.75 g, 80%) which was of sufficient purity for use in the subsequent reaction.

Workup

  1. customwas formed
  2. temperaturethe resulting mixture heated
  3. temperatureto reflux a total of 24 hours
  4. temperatureThe mixture was cooled to room temperature
  5. customto 0° C. to give a precipitate
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-04908d49d6934560b16e615cd681b2f0
Source dataset
uspto-grants-1990_01
Patent number
US04895861

Reaction notes

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